1-(2,5-二甲基-1-苯基-1H-吡咯-3-基)乙烷-1-酮 | 105357-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-(2,5-二甲基-1-苯基-1H-吡咯-3-基)乙烷-1-酮
• 英文名称: 1-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethan-1-one
• 英文别名: 1-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-ethanone；1-(2,5-Dimethyl-1-phenylpyrrol-3-yl)ethanone
• CAS: 105357-89-9
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: JOOMTMQCSPCJKK-UHFFFAOYSA-N

物化性质

• 沸点：
  350.5±37.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2,5-二甲基-1-苯基-1H-吡咯-3-基)乙烷-1-酮 在 氨 作用下， 以 四氢呋喃 为溶剂， 生成 (3E)-3-[1-(2,5-dimethyl-1-phenylpyrrol-3-yl)ethylidene]-4-propan-2-ylidenepyrrolidine-2,5-dione
  参考文献：
  名称：

  Photochromic Cyan Dyes of Fulgide Derivatives in Polymer Film

  摘要：

  掺杂了3-4 wt%的富勒烯衍生物的光致变色聚合物薄膜具有很高的热和光化学疲劳阻力，以及良好的颜色特性，可用作可擦写彩色显示和印刷材料的青色染料。

  DOI：

  10.1246/cl.2005.574
• 作为产物：
  描述：

  3-(1-phenylamino-ethylidene)-hex-5-yn-2-one 在 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 0.02h， 以78%的产率得到1-(2,5-二甲基-1-苯基-1H-吡咯-3-基)乙烷-1-酮
  参考文献：
  名称：

  Silver-catalysed hydroamination: synthesis of functionalised pyrroles

  摘要：

  It has been shown that functionalised pyrroles can be efficiently prepared using a two-step sequence. This sequence involves the propargylation of secondary enaminones using n-BuLi and propargyl bromide, followed by intramolecular hydroamination catalysed by silver nitrate. The hydroamination can be carried out at room temperature (overnight) or in a domestic microwave oven (60s). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.019

文献信息

• Efficient synthesis of highly substituted pyrroles through a Pd(OCOCF3)2-catalyzed cascade reaction of 2-alkenal-1,3-dicarbonyl compounds with primary amines
  作者：Wei Yang、Liliang Huang、Hong Liu、Wei Wang、Hao Li

  DOI：10.1039/c3cc42216j

  日期：——

  We describe an unprecedented Pd(OCOCF3)2-catalyzed cascade process for the synthesis of highly functionalized 1,2,3,5-tetrasubstituted pyrroles with high efficiency. Unlike documented methods relying on preformed enamines and active halogenated terminal alkenes, the process employs simple 2-alkenal-dicarbonyls and primary amines in ‘one-pot’.

  我们描述了一种前所未有的Pd(OCOCF3)2催化级联过程，用于高效合成高度官能化的1,2,3,5-四取代吡咯。与依赖预形成的烯胺和活性卤代末端烯烃的已知方法不同，该过程采用简单的2-烯醛二羰基化合物和一级胺在“一锅法”中进行。
• Efficient synthesis of substituted pyrroles through iron-mediated oxidation reaction of 3-methylenehexane-2,5-dione with primary amines
  作者：Xi Chen、JiaCheng Yuan、Min Zhou

  DOI：10.1080/00397911.2018.1533972

  日期：2019.1.2

  Abstract An efficient route has been developed for the synthesis of multiple substituted pyrrole derivatives from the readily available agents through iron-mediated oxidative aromatization process in good to excellent yields. This method is well tolerated with a diverse broad range of substrates and a complementary approach to currently available synthetic methods. GRAPHICAL ABSTRACT

  摘要 已经开发了一种有效的路线，用于从易得的试剂通过铁介导的氧化芳构化过程合成多取代的吡咯衍生物，收率良好。这种方法可以很好地耐受各种底物，并且是目前可用合成方法的补充方法。图形概要
• Synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives from 2-(2-bromoallyl)-1,3-dicarbonyl compounds
  作者：Ayhan S Demir、Idris M Akhmedov、Özge Sesenoglu

  DOI：10.1016/s0040-4020(02)01298-x

  日期：2002.12

  2-(2-Bromoallyl)-1,3-dicarbonyl compounds are converted into β-enamino, β-hydrazino esters and ketones, followed by base-promoted cyclization, leading to the formation of the corresponding 1,2,3,5-tetrasubstituted pyrroles. 1,2,4- and 1,2,3,4-Substituted pyrroles are also isolated as minor products. Starting from the 2-(2-bromoallyl)-cyclohexane-1,3-dione the corresponding tetrahydro indolone is prepared

  将2-（2-溴烯丙基）-1,3-二羰基化合物转化为β-烯氨基，β-肼基酸酯和酮，然后进行碱促进的环化反应，从而形成相应的1,2,3,5-四取代吡咯。1,2,4-和1,2,3,4-取代的吡咯也作为次要产物被分离出来。从2-（2-溴烯丙基）-环己烷-1，3-二酮开始，以高收率制备相应的四氢吲哚酮。
• Gold‐Catalyzed Sequential Amination/Annulation Reactions of 2‐Propynyl‐1,3‐dicarbonyl Compounds
  作者：Antonio Arcadi、Sabrina Di Giuseppe、Fabio Marinelli、Elisabetta Rossi

  DOI：10.1002/1615-4169(200107)343:5<443::aid-adsc443>3.0.co;2-#

  日期：2001.7

  The gold(III)-catalyzed sequential amination/annulation reaction of 2-propynyl-1,3-dicarbonyl compounds 1 with primary amines 2 produces 1,2,3,5-substituted pyrroles 4 in moderate to high yields.
• Water-Mediated Strecker Reaction: An Efficient and Environmentally Friendly Approach for the Synthesis of <font>α</font>-Aminonitriles <i>via</i> a Three-Component Condensation
  作者：Samikannu Ramesh、Kulanthaivel Sivakumar、Chiradeep Panja、Pirama Nayagam Arunachalam、Appaswami Lalitha

  DOI：10.1080/00397910903457381

  日期：2010.11.3

  The synthesis of -aminonitriles by a direct three component Strecker reaction has been achieved in water, which is found to be an inexpensive, non-toxic and eco-friendly reaction medium for the nucleophilic addition. This protocol is effective to a wide variety of substrates with different functional groups and does not require the use any other catalyst.